Interviewing for leadership positions

Siddharth Ram
The CTO’s toolbox
4 min readFeb 16, 2022

In how to hire I shared the practices I use for hiring. My preference is to ask candidates to work on a take home problem, and then base the interview on how they approached solving the problem. It is similar for leadership positions as well.

When the interviews are for more senior positions the take home problem becomes more ambiguous. It is not about solving a particular technical problem: at leadership levels, it is overweighted on your true north, your leadership style and where your energies are. There is no black and white ‘you did it in O(n²)‘ kind of truthiness. There is a lot more nuance.

Here is an actual case study that I ask Director of Engineering candidates (or higher) to work on:

Case Study

About this document:
This document represents a take home assignment that will form the basis of this interview. The goal is to make sure you have time to think about the problem statement and share out your approach to solving the problem

Some guidelines for presenting:
1.Please start by introducing yourself — we will include a number of people who don’t know who you are before the interview
2.Please make any assumptions necessary to build out the scenario. The scenario is deliberately open ended. State the assumptions you have made.
3.The presentation will constitute the basis for deep dives with the team. The Craft demo is your time — only time we will interrupt you is to ask clarifying questions

The scenario
Abacus Inc.
is a company that specializes in learning and development in young children (3–8).
The company is a decade old. They have two main product lines:
1) A line of internet connected toys that get new behaviour downloaded to them
2) Online educational software that helps children learn by playing online games.
You have been hired to lead application development covering both product lines. The CEO has the following concerns that she’d like you to address

1.Remote work. The team is distributed across multiple geographies. She feels that there is inadequate communication and difficulty maintaining Abacus’ culture across multiple geos (Abacus has developers in China, Chile and the UK)
2. Productivity. She wants to understand productivity and how it can be improved
3. Pace. She is unhappy with the pace of development. Even though the company is cloud based, she feels that the best companies in the world move much faster than Abacus does — in fact, Abacus is falling behind its competitors on the speed at which releases take place. She wonders if we need to further modernize technology. The CTO pops in
at this time and shares that ..’Abacus uses state of the art, scalable EC2 instances and we even deploy every two weeks.’ He disagrees that pace is a problem.
4.The Analytics pipeline. Currently, there are separate leaders for the toys line and the online games with separate teams (including separate business development and product management teams). Data is stored in multiple databases (Postgres, SQL Server, MongoDB, TimeSeries DB). They are moved into a data warehouse using standard ETL stored procedures. Unfortunately, data moves only once every 24 hours, disallowing ‘real time’ decisioning. Even worse, the visualization tool requires specialized knowledge in order to build dashboards. The CEO wants self service dashboards
5.API’s. They are fragmented and inconsistent. Though there is a written down policy on API’s, there is little governance. Consequently, customers/partners who integrate via API’s are a discontent lot
6.Front End development. Much of the front end development is server side. The CEO has heard that Client side development is all the rage and wants to move to it.

Her directions to you are ‘Figure out all these problems. Come back with a plan. Let me know what is needed to implement the plans. Since I am an Engineer, I would like to see the technical details as well.’

The case study is deliberately very open ended, covering everything from culture, technology and process. There is really no right and wrong in what we are looking for — we are looking for how the candidate approaches problem solving, their ability to present a cogent case for the problem space and its solution. This leads to a detailed discussion of the pros and cons.

Several things surprise me about these interviews, where many candidates fail to do well.

The first mistake is not spending time thinking about the problem. You have to really understand the problem space to build out a solution.

The second mistake is leading with where you energies are at. If you are a deep technologist and you ignore other parts of the problem altogether, you are going to miss the mark

The final common problem is not taking the time to actually read the instructions. For example, the very first line is ‘start by introducing yourself’ — and it astonishes me how many choose to bypass this altogether, losing out on a chance to create a real connection with the audience.

How would you go about presenting a solution to this case study? Send me a response and you could be in line for an interview at Inflection!

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